#193 - Q&A edition...Social Security lump sum for retroactive payments, whether to pay off a mortgage, step-up in basis, gifting without having to file a gift tax return and MORE!

Listener Q&A where Andy talks about: Income tax treatment of buying bonds in a normal non-qualified brokerage account when you buy or sell bonds in between coupon periods ( 8:37 )When still working, are 50 or older, are maxing out your 401(k) contributions, and are high income and therefore would need to have your catch-up contribution go into your Roth (instead of pre-tax) 401(k), would it be better to skip the catch-up and instead put that money in a normal brokerage account ( 14:40 )Taxation of Social Security lump sums received for prior month's retroactive payments; is it taxable in the year received or in the prior year that the payments were attributable to ( 17:56 )Does the imputed wage income from employer group life insurance in excess of $50,000 death benefit qualify as earned income for purposes of making Roth IRA contributions ( 24:26 )Deciding how/when to sell out of appreciated assets in a brokerage account you no longer want but don't want to have to deal with realizing taxable gains ( 29:11 )Thoughts on direct indexing, and whether it's a strategy worth considering ( 37:01 )Whether or not to pay off a mortgage, especially now that interest rates are higher than they were a few years ago ( 44:07 )Thoughts on when to stop saving if/when you've saved "enough," balancing planning for the future you vs the present you, deciding how much to sacrifice now for saving for the future, etc. ( 49:24 )The differences in step-up in basis rules for spouses in community property states vs common law states, and how that impacts federal taxes (even if the gains aren't taxable at the state level) ( 55:10 )What to keep in mind when spouses want to maximize gift giving and not have to file a gift tax return ( 1:01:44 )Deductibility of donating appreciated securities vs cash and how to plan large donations in years of doing Roth conversions to help manage taxable income ( 1:07:47 )To send Andy questions to be addressed on future Q&A episodes, email [email protected] in this episode:My company newsletter - Retirement Planning InsightsFacebook group - Retirement Planning Education (formerly Taxes in Retirement)YouTube channel - Retirement Planning Education (formerly Retirement Planning Demystified)Retirement Planning Education website - www.RetirementPlanningEducation.com